Esters of carboxylarylphosphoric acids.



EYIQITED @TLATES PATEN MAX ENGELMANN, OF ELB'EB'FELD, GERMANY, ASSIGNOR TO SYNTHETIC PATENTS CO.

INC., OF NEXV YORK, N. Y., A CORPORATION OF NEW? YDRK.

ESTERS OF CARBOXYLARYLPHOSPHORIC ACIDS.

No Drawing.

i Y i cooca-mooces toocms g coocauocm 3 7 crown oroionn ormoim i CH? l 1 l l l -coocan 1 l \l 2 5 coocmisog coocmcan etc., have proved to ,be valuable remedies against lnfectious diseases. 'lhese esters have the following general tormula:

where R is the aryl or other estenforrning group, 6. g. phenyl, nitro-phenyl. methoxyphenyl, benzyl, guaiacyl, etc. When made from para-oxybcnzoic acid derivatives they have the following general formula:

where R has-the same meaning as in the preceding formula. The new esters are generally crystalline colorless products, soluble in alcohol and ether and ditticultly soluble in water but forming metal salts, such as salts of potassium, sodium, calcium, copper, silver, etc., which are generally soluble in Water.

My new products can be obtained in the following way: By the action of phosphorus gen-carbonylarylphosphoric acid halids are Specification of Letters Patent.

halogenids -'upon aromatic oxyacids llalo- Patented Jam 15), sets,

Application filed May 12, 1914. Serial No. 838,112.

obtained e. g. from para-oxybenzoic acid. and phosphorus pentachlorid the product:

By the action of these halogenids upon alcohols, phenols, phenolalcohols, oxyacids, etc, the new compounds are obtained.

In order to illustrate the new process more fully the following example is given, the

until a strong alkaline reaction and the dimetl'iylanilin is removed with ether. The solution-treated with ether is then very strongly acidulated with dilated sulfuric 8;) acid and the para-gual'acol-carboxylphcuyh phosphoric acid which separates hereby in a crystalline shape rsfiltered off and pur'lfied by a crystallization from dilute alcohol.

It crystallizes in needles melting at 182 CL and is soluble in alcohol and Water. The acid is precipitated from aqueous solutions by the addition of hydrochloric acid. This product has in the shape of its disodium sa t which is easily soluble in Water most proh- I ably the following fornzfilaz l: In an analogousmianner other of the above mentioned esters are obtained e. g. the

isoeresolester of para--carboxylphenylphoshorie acid melting at 1T9 (L; "the tliymol- 'ster ofpara-carboxylphenylphosphorie acid ioeltin gat 163 C.

claim: i 'Flie. new esters derived "from the car- Wflpliosplioric acids which are generall C1' \St.alllnc. odorless products soluble in alcohol and. dill'eultly soluble in water but forming metal salts which are mostly soluble in wat r and being valuable therapeutics against infectious diseases, substantially as files i 'bed.

2. The new esters of carboxylarylphosphoric acids of the following general formula:

' substantiall as :escribed.

Z5. 'lhe new esters of :arboXylarylphosi: we acids 0!; the 'l'ollowing general forwhere R is an aromatic ester-forming group,

which esters are generally crystalline products soluble in alcohol and dillieultly soluble in water but forming metal salts which are mostly soluble in water and which are valuable therapeutics against infectious diseases, substantially as described.

4. The new guaiacol ester of the carboxylphenylphosphoric acid having most probably in the shape of'its sodium salt thefon mnla:

which crystallizes in needles melting at 182 (L. soluble in alcohol and dillicultly solulile in water but easily soluble in water in the shape of its disodium salt and being a valuable remedy against infectious diseases, sub-- stantially as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

MAX ENGELMANN. [L.s.

Witnesses llicuax Norma, Fnaxces N uricn. 

